Triethylsilane → (2S)-3-(4-Benzyloxy-2-methyl-phenyl)-2-ethoxy-propionic acid methyl ester

Triethylsilane (23 ml, 145 mmol) was added to a vigorously stirred, ice-cooled solution of (2S,3R)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester (5 g, 14.5 mmol) in trifluoroacetic acid (84 ml) under an argon atmosphere. The mixture was stirred at 0° C. for 30 min and for additional 2 h at ambient temperature. The solution was poured onto crashed ice and extracted with ethyl acetate. The organic layer was washed two times with water and neutralized with saturated aqueous sodium bicarbonate solution. The ethyl acetate layer was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to give a colorless oil which was purified by column chromatography (silica gel, cyclohexane/AcOEt) to yield 2.15 g (6.5 mmol, 45%) of the title compound as colorless oil.

1. stirringThe mixture was stirred at 0° C. for 30 min and for additional 2 h at ambient temperature
2. additionThe solution was poured
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed two times with water
5. washThe ethyl acetate layer was washed with brine
6. dry with materialdried over sodium sulfate
7. customThe solvent was removed under reduced pressure
8. customto give a colorless oil which
9. customwas purified by column chromatography (silica gel, cyclohexane/AcOEt)

ORD record

ord-5cf0ee9b9e954117817e200cf0a0bb43

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348349B2